HCID 60028532, compound → HCID 58099974, compound

HRID 1038792Notes

Reaction equation

HRID 1038792 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=O)[CH2:13][CH2:12][C:11]2=O)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])([O-:3])=[O:2]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)=[CH:6][C:5]=1[C:17]([F:20])([F:18])[F:19])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 60028532HCID 60028532, compound

Product 1

HCID 58099974HCID 58099974, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine-2,5-dione (400 mg, 1.39 mmol) in THF (10 mL) was added BH3 (1.39 mL of 1 M in THF, 1.39 mmol) dropwise. The reaction mixture was then refluxed under N2 atmosphere for 16 h. The reaction was cooled, quenched with methanol, and concentrated in vacuo to provide 1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine as a yellow solid (360 mg, quantitative yield). M+H m/z 261.1.

Workup

  1. temperatureThe reaction mixture was then refluxed under N2 atmosphere for 16 h
  2. temperatureThe reaction was cooled
  3. customquenched with methanol
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-429f68f3cfec478b8a163b3a677fdebd
Source dataset
uspto-grants-2013_10
Patent number
US08552006B2

Reaction notes

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